N'-[(E)-(3-Fluoro-pyridin-2-yl)methyl-idene]benzohydrazide monohydrate.

The title compound, C(13)H(10)FN(3)O·H(2)O, exists in the E conformation with respect to the azomethane C=N double bond. The mol-ecule is close to planar with a maximum deviation of 0.286 (2) Å. The pyridine ring is essentially coplanar with the central C(= O)N(2)C unit [dihedral angle = 2.02 (3)°] and the phenyl ring exhibits a dihedral angle of 14.41 (10)° with respect to the central unit. The crystal structure features O-H⋯N, N-H⋯O and O-H⋯O hydrogen-bond inter-actions between the solvent water and the benzohydrazide mol-ecules, as well as C-H⋯O hydrogen bonds and C-F⋯π [3.0833 (18) Å] inter-actions.

Related literature

For background to the use of benzohydrazides as catalysts, see: Heravi et al. (2007 ▶); Hou et al. (2005 ▶) and for their biological activity, see: Sreeja et al. (2004 ▶). For the synthesis of related compounds, see: Fun et al. (2008 ▶). For related structures, see Mangalam et al. (2009 ▶).

Experimental

Crystal data

C13H10FN3O·H2O

M = 261.26

Orthorhombic,

a = 8.2540 (4) Å

b = 11.5489 (4) Å

c = 26.1962 (11) Å

V = 2497.14 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.964, T max = 0.974

34264 measured reflections

2192 independent reflections

1817 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.096

S = 1.07

2190 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035179/zl2494sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035179/zl2494Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035179/zl2494Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H10FN3O·H2O	F(000) = 1088
Mr = 261.26	Dx = 1.390 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9884 reflections
a = 8.2540 (4) Å	θ = 5.8–54.5°
b = 11.5489 (4) Å	µ = 0.11 mm−1
c = 26.1962 (11) Å	T = 296 K
V = 2497.14 (18) Å3	Block, colorless
Z = 8	0.35 × 0.30 × 0.25 mm

Bruker Kappa APEXII CCD diffractometer	2192 independent reflections
Radiation source: fine-focus sealed tube	1817 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scan	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
Tmin = 0.964, Tmax = 0.974	k = −13→13
34264 measured reflections	l = −31→31

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0425P)2 + 0.6736P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2190 reflections	Δρmax = 0.18 e Å−3
185 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0073 (8)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
F1	0.75071 (13)	0.87133 (8)	1.09485 (3)	0.0629 (3)
O1	0.82638 (15)	1.12491 (9)	0.86590 (4)	0.0561 (3)
O1W	0.90084 (17)	0.73757 (10)	0.93534 (6)	0.0600 (3)
N1	0.60294 (15)	1.12483 (10)	1.03176 (5)	0.0462 (3)
N2	0.79363 (14)	1.02906 (10)	0.95707 (4)	0.0413 (3)
N3	0.88214 (15)	0.97616 (11)	0.91928 (4)	0.0418 (3)
C1	0.51707 (19)	1.17020 (13)	1.06961 (6)	0.0514 (4)
H1	0.4633	1.2397	1.0637	0.062*
C2	0.5032 (2)	1.12006 (14)	1.11710 (6)	0.0562 (4)
H2	0.4420	1.1552	1.1425	0.067*
C3	0.5812 (2)	1.01773 (15)	1.12616 (6)	0.0557 (4)
H3	0.5742	0.9811	1.1577	0.067*
C4	0.66988 (18)	0.97122 (13)	1.08709 (5)	0.0444 (4)
C5	0.68155 (16)	1.02434 (11)	1.04024 (5)	0.0392 (3)
C6	0.77636 (17)	0.97353 (12)	0.99866 (5)	0.0416 (3)
H6	0.8237	0.9010	1.0026	0.050*
C7	0.89290 (17)	1.03168 (12)	0.87370 (5)	0.0416 (3)
C8	0.99453 (17)	0.97527 (13)	0.83362 (5)	0.0427 (3)
C9	1.0457 (2)	0.86099 (14)	0.83555 (6)	0.0543 (4)
H9	1.0176	0.8148	0.8633	0.065*
C10	1.1385 (2)	0.81533 (17)	0.79643 (6)	0.0664 (5)
H10	1.1715	0.7384	0.7978	0.080*
C11	1.1819 (2)	0.88324 (18)	0.75569 (7)	0.0692 (5)
H11	1.2441	0.8522	0.7294	0.083*
C12	1.1337 (2)	0.99666 (18)	0.75360 (6)	0.0650 (5)
H12	1.1645	1.0427	0.7261	0.078*
C13	1.03959 (19)	1.04278 (15)	0.79213 (6)	0.0529 (4)
H13	1.0062	1.1196	0.7903	0.064*
H3'	0.908 (2)	0.9010 (16)	0.9235 (6)	0.057 (5)*
H1A	0.838 (3)	0.699 (2)	0.9166 (9)	0.102 (9)*
H1B	0.902 (3)	0.701 (2)	0.9653 (9)	0.100 (8)*

	U11	U22	U33	U12	U13	U23
F1	0.0738 (6)	0.0639 (6)	0.0511 (5)	0.0185 (5)	0.0040 (5)	0.0128 (4)
O1	0.0757 (8)	0.0461 (6)	0.0467 (6)	0.0037 (5)	0.0021 (5)	0.0061 (5)
O1W	0.0761 (8)	0.0452 (6)	0.0589 (8)	−0.0080 (6)	0.0070 (7)	0.0081 (6)
N1	0.0496 (7)	0.0422 (7)	0.0468 (7)	0.0015 (5)	0.0020 (6)	−0.0028 (5)
N2	0.0454 (7)	0.0418 (6)	0.0366 (6)	−0.0004 (5)	0.0024 (5)	−0.0031 (5)
N3	0.0500 (7)	0.0406 (7)	0.0348 (6)	0.0017 (5)	0.0046 (5)	−0.0004 (5)
C1	0.0508 (9)	0.0451 (8)	0.0583 (10)	0.0016 (7)	0.0051 (7)	−0.0096 (7)
C2	0.0529 (9)	0.0628 (10)	0.0528 (10)	−0.0014 (8)	0.0107 (7)	−0.0155 (8)
C3	0.0571 (9)	0.0704 (11)	0.0395 (8)	−0.0017 (8)	0.0053 (7)	−0.0008 (7)
C4	0.0447 (8)	0.0492 (8)	0.0395 (8)	0.0006 (7)	−0.0027 (6)	−0.0008 (6)
C5	0.0381 (7)	0.0417 (7)	0.0377 (7)	−0.0032 (6)	−0.0013 (6)	−0.0039 (6)
C6	0.0459 (8)	0.0401 (8)	0.0388 (7)	0.0034 (6)	−0.0001 (6)	−0.0008 (6)
C7	0.0458 (8)	0.0415 (8)	0.0375 (8)	−0.0089 (6)	−0.0036 (6)	−0.0003 (6)
C8	0.0421 (8)	0.0527 (8)	0.0333 (7)	−0.0109 (6)	−0.0020 (6)	−0.0007 (6)
C9	0.0643 (10)	0.0551 (9)	0.0433 (8)	−0.0037 (8)	0.0112 (8)	−0.0003 (7)
C10	0.0736 (12)	0.0708 (11)	0.0550 (10)	0.0039 (9)	0.0161 (9)	−0.0077 (9)
C11	0.0611 (11)	0.1001 (15)	0.0463 (10)	−0.0034 (10)	0.0143 (8)	−0.0098 (10)
C12	0.0576 (10)	0.0987 (14)	0.0386 (9)	−0.0147 (10)	0.0058 (7)	0.0105 (9)
C13	0.0519 (9)	0.0651 (10)	0.0418 (8)	−0.0110 (8)	−0.0024 (7)	0.0068 (7)

F1—C4	1.3481 (17)	C4—C5	1.376 (2)
O1—C7	1.2258 (17)	C5—C6	1.4639 (19)
O1W—H1A	0.84 (3)	C6—H6	0.9300
O1W—H1B	0.89 (2)	C7—C8	1.494 (2)
N1—C1	1.3266 (19)	C8—C9	1.387 (2)
N1—C5	1.3480 (18)	C8—C13	1.388 (2)
N2—C6	1.2721 (18)	C9—C10	1.384 (2)
N2—N3	1.3736 (16)	C9—H9	0.9300
N3—C7	1.3582 (18)	C10—C11	1.372 (3)
N3—H3'	0.901 (18)	C10—H10	0.9300
C1—C2	1.377 (2)	C11—C12	1.370 (3)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.366 (2)	C12—C13	1.381 (2)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.368 (2)	C13—H13	0.9300
C3—H3	0.9300
H1A—O1W—H1B	105 (2)	C5—C6—H6	120.2
C1—N1—C5	118.31 (13)	O1—C7—N3	122.14 (13)
C6—N2—N3	116.90 (12)	O1—C7—C8	121.16 (13)
C7—N3—N2	117.28 (12)	N3—C7—C8	116.67 (13)
C7—N3—H3'	123.2 (11)	C9—C8—C13	118.79 (14)
N2—N3—H3'	117.8 (11)	C9—C8—C7	124.09 (13)
N1—C1—C2	123.60 (15)	C13—C8—C7	117.12 (14)
N1—C1—H1	118.2	C10—C9—C8	120.27 (15)
C2—C1—H1	118.2	C10—C9—H9	119.9
C3—C2—C1	118.79 (14)	C8—C9—H9	119.9
C3—C2—H2	120.6	C11—C10—C9	120.18 (18)
C1—C2—H2	120.6	C11—C10—H10	119.9
C2—C3—C4	117.49 (15)	C9—C10—H10	119.9
C2—C3—H3	121.3	C12—C11—C10	120.13 (17)
C4—C3—H3	121.3	C12—C11—H11	119.9
F1—C4—C3	119.21 (13)	C10—C11—H11	119.9
F1—C4—C5	118.78 (13)	C11—C12—C13	120.19 (16)
C3—C4—C5	122.00 (14)	C11—C12—H12	119.9
N1—C5—C4	119.81 (13)	C13—C12—H12	119.9
N1—C5—C6	118.68 (12)	C12—C13—C8	120.43 (16)
C4—C5—C6	121.51 (13)	C12—C13—H13	119.8
N2—C6—C5	119.67 (12)	C8—C13—H13	119.8
N2—C6—H6	120.2
C6—N2—N3—C7	176.10 (12)	N2—N3—C7—O1	−0.4 (2)
C5—N1—C1—C2	−0.2 (2)	N2—N3—C7—C8	177.81 (11)
N1—C1—C2—C3	−0.2 (2)	O1—C7—C8—C9	−166.31 (14)
C1—C2—C3—C4	0.3 (2)	N3—C7—C8—C9	15.5 (2)
C2—C3—C4—F1	178.90 (14)	O1—C7—C8—C13	13.8 (2)
C2—C3—C4—C5	0.1 (2)	N3—C7—C8—C13	−164.45 (13)
C1—N1—C5—C4	0.6 (2)	C13—C8—C9—C10	−0.7 (2)
C1—N1—C5—C6	179.89 (13)	C7—C8—C9—C10	179.37 (15)
F1—C4—C5—N1	−179.40 (12)	C8—C9—C10—C11	0.7 (3)
C3—C4—C5—N1	−0.5 (2)	C9—C10—C11—C12	0.1 (3)
F1—C4—C5—C6	1.4 (2)	C10—C11—C12—C13	−0.8 (3)
C3—C4—C5—C6	−179.78 (14)	C11—C12—C13—C8	0.8 (3)
N3—N2—C6—C5	−179.18 (11)	C9—C8—C13—C12	0.0 (2)
N1—C5—C6—N2	5.7 (2)	C7—C8—C13—C12	179.90 (14)
C4—C5—C6—N2	−175.10 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3′···O1W	0.901 (18)	1.914 (18)	2.7917 (17)	164.3 (16)
O1W—H1A···O1i	0.84 (3)	2.08 (3)	2.9187 (19)	172 (2)
O1W—H1A···N2i	0.84 (3)	2.48 (2)	2.9494 (17)	116.1 (19)
O1W—H1B···N1i	0.89 (2)	1.95 (3)	2.8420 (18)	178 (2)
C9—H9···O1W	0.93	2.30	3.209 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3′⋯O1W	0.901 (18)	1.914 (18)	2.7917 (17)	164.3 (16)
O1W—H1A⋯O1i	0.84 (3)	2.08 (3)	2.9187 (19)	172 (2)
O1W—H1A⋯N2i	0.84 (3)	2.48 (2)	2.9494 (17)	116.1 (19)
O1W—H1B⋯N1i	0.89 (2)	1.95 (3)	2.8420 (18)	178 (2)
C9—H9⋯O1W	0.93	2.30	3.209 (2)	165

Symmetry code: (i) .